Electrophotographic photoreceptor, electrophotographic image forming method, electrophotographic image forming apparatus, electrophotographic process cartridge

Abstract

An electrophotographic photoreceptor including a conductive substrate and a photosensitive layer overlying the conductive substrate. The photosensitive layer comprises a phthalimide isoindole derivative having a specific chemical formula.

1. An electrophotographic photoreceptor, comprising:
 a conductive substrate; and 
 a photosensitive layer overlying the conductive substrate, and comprising a phthalimide isoindole derivative having the following formula (1): 
 
       
         
           
           
               
               
           
         
       
       wherein each of R 1 , R 2 , R 3 , and R 4  independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, a halogen atom, or a nitro group; each of k and l independently represents an integer of from 1 to 4; and each of m and n independently represents an integer of from 1 to 5. 
     
     
       2. The electrophotographic photoreceptor according to  claim 1 , wherein the electrophotographic photoreceptor is chargeable to both positive and negative polarities. 
     
     
       3. The electrophotographic photoreceptor according to  claim 1 , wherein the photosensitive layer further comprises a charge transport material. 
     
     
       4. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a derivative having the following formula (2): 
       
         
           
           
               
               
           
         
       
       wherein X represents a single bond or a vinylene group; R 1  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; R 5  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Ar 1  and R 5  may share ring connectivity to form a ring; A represents a substituted or unsubstituted phenyl group having the following formula (3), a substituted or unsubstituted naphthyl group having the following formula (4), 9-anthryl group, or a substituted or unsubstituted carbazolyl group: 
       
         
           
           
               
               
           
         
       
       wherein R 2  represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a group having the following formula (5): 
       
         
           
           
               
               
           
         
       
       wherein each of R 3  and R 4  independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group; R 3  and R 4  may share ring connectivity to form a ring; m represents an integer of from 1 to 3; and when m is 2 or more, multiple R 2  may be, but need not necessarily be, the same. 
     
     
       5. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a triarylamine derivative having the following formula (6): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1 , R 3 , and R 4  independently represents a hydrogen atom, an amino group, an alkoxy group, a thioalkoxy group, an aryloxy group, a methylenedioxy group, a substituted or unsubstituted alkyl group, a halogen atom, or a substituted or unsubstituted aromatic hydrocarbon group; R 2  represents a hydrogen atom, an alkoxy group, a substituted or unsubstituted alkyl group, or a halogen atom; each of k, l, m, and n independently represents an integer of from 1 to 4; and when each of k, l, m, and n is 2 or more, multiple R 1 , R 2 , R 3 , and R 4  may be, but need not necessarily be, the same. 
     
     
       6. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is an arylamine derivative having the following formula (7): 
       
         
           
           
               
               
           
         
       
       wherein X represents a single bond or a vinylene group; R 1  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Ar 1  represents a substituted or unsubstituted aromatic hydrocarbon group; R 3  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Ar 1  and R 3  may share ring connectivity to form a ring; Ar 2  represents a substituted or unsubstituted phenylene group having the following formula (8) or a substituted or unsubstituted naphthylene group having the following formula (9): 
       
         
           
           
               
               
           
         
       
       wherein R 2  represents a hydrogen atom, an alkyl group, an alkoxy group, or a halogen atom; m represents an integer of from 1 to 3; when m is 2 or more, multiple R 2  may be, but need not necessarily be, the same; and R 4  represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group. 
     
     
       7. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a vinyl-group-containing aromatic hydrocarbon derivative having the following formula (10): 
       
         
           
           
               
               
           
         
       
       wherein X represents a single bond or a vinylene group; R 1  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; Ar 1  represents a substituted or unsubstituted divalent aromatic hydrocarbon group; R 5  represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group; A represents a substituted or unsubstituted phenyl group having the following formula (3), a substituted or unsubstituted naphthyl group having the following formula (4), 9-anthryl group, or a substituted or unsubstituted carbazolyl group: 
       
         
           
           
               
               
           
         
       
       wherein R 2  represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, or a group having the following formula (5): 
       
         
           
           
               
               
           
         
       
       wherein each of R 3  and R 4  independently represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aromatic hydrocarbon group; R 3  and R 4  may share ring connectivity to form a ring; m represents an integer of from 1 to 3; and when m is 2 or more, multiple R 2  may be, but need not necessarily be, the same. 
     
     
       8. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a diphenoquinone derivative having the following formula (14): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1  and R 2  independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group. 
     
     
       9. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a naphthoquinone derivative having the following formula (15): 
       
         
           
           
               
               
           
         
       
       wherein R 1  represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group; R 2  represents a substituted or unsubstituted alkyl group, a substituted or unsubstituted aromatic hydrocarbon group, or a group having the following formula (16):
   —O—R 3   (16)
 
 wherein R 3  represents a substituted or unsubstituted alkyl group or a substituted or unsubstituted aryl group. 
 
     
     
       10. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a naphthalenetetracarboxylic acid derivative having the following formula (17): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1  and R 2  independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group. 
     
     
       11. The electrophotographic photoreceptor according to  claim 3 , wherein the charge transport material is a naphthalenetetracarboxylic acid dimer derivative having the following formula (18): 
       
         
           
           
               
               
           
         
       
       wherein each of R 1  and R 2  independently represents a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aromatic hydrocarbon group. 
     
     
       12. The electrophotographic photoreceptor according to  claim 1 , wherein the photosensitive layer has a multilayer structure comprising:
 a charge generation layer; and 
 a charge transport layer overlying the charge generation layer. 
 
     
     
       13. The electrophotographic photoreceptor according to  claim 1 , wherein the photosensitive layer has a multilayer structure comprising:
 a charge transport layer; and 
 a charge generation layer overlying the charge transport layer. 
 
     
     
       14. The electrophotographic photoreceptor according to  claim 1 , wherein the photosensitive layer is a single layer. 
     
     
       15. An electrophotographic image forming method, comprising:
 charging the electrophotographic photoreceptor according to  claim 1 ; 
 irradiating the charged photoreceptor with light containing image information to form an electrostatic latent image thereon; 
 developing the electrostatic latent image with a toner to form a toner image; and 
 transferring the toner image from the photoreceptor onto a transfer material. 
 
     
     
       16. The electrophotographic image forming method according to  claim 15 , wherein the light containing image information is emitted from a laser diode or a light-emitting diode. 
     
     
       17. An electrophotographic image forming apparatus, comprising:
 the electrophotographic photoreceptor according to  claim 1  that bears an electrostatic latent image; 
 a charger that charges the photoreceptor; 
 an irradiator that irradiates the charged photoreceptor with light containing image information to form an electrostatic latent image thereon; 
 a developing device that develops the electrostatic latent image with a toner to form a toner image; and 
 a transfer device that transfers the toner image from the photoreceptor onto a transfer material. 
 
     
     
       18. The electrophotographic image forming apparatus according to  claim 17 , wherein the irradiator is a laser diode or a light-emitting diode. 
     
     
       19. An electrophotographic process cartridge detachably mountable on image forming apparatus, comprising:
 the electrophotographic photoreceptor according to  claim 1  that bears an electrostatic latent image; and 
 at least one of a charger that charges the photoreceptor, a developing device that develops the electrostatic latent image into a toner image, and a cleaning device that removes residual toner particles remaining on the photoreceptor after transferring a toner image therefrom.